Palladium-Catalyzed Pyrazole-Directed sp 3 C-H Bond Arylation for the Synthesis of β-Phenethylamines

We have developed a method for palladium-catalyzed, pyrazole-directed sp C-H bond arylation by aryl iodides. The reaction employs a Pd(OAc) catalyst at 5-10 mol % loading and silver(I) oxide as a halide-removal agent, and it proceeds in acetic acid or acetic acid/hexafluoroisopropanol solvent. Ozono...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-03, Vol.56 (13), p.3630-3634
Main Authors: Gulia, Nurbey, Daugulis, Olafs
Format: Article
Language:English
Subjects:
Catalysis
Iodides - chemical synthesis
Iodides - chemistry
Oxides - chemistry
Palladium - chemistry
Phenethylamines - chemical synthesis
Phenethylamines - chemistry
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Silver Compounds - chemistry
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Summary:We have developed a method for palladium-catalyzed, pyrazole-directed sp C-H bond arylation by aryl iodides. The reaction employs a Pd(OAc) catalyst at 5-10 mol % loading and silver(I) oxide as a halide-removal agent, and it proceeds in acetic acid or acetic acid/hexafluoroisopropanol solvent. Ozonolysis of the pyrazole moiety affords pharmaceutically important β-phenethylamines.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201611407